


Sam Winchester Cries During Sex

by AndreaDTX



Category: Supernatural
Genre: Angst, Character Study, Exploration of sexuality, F/M, Hopeful Ending, M/M, POV Sam Winchester, Pre-Series, Sam Winchester is a badass, not exactly sure how to tag this, somewhat dark
Language: English
Status: Completed
Published: 2020-02-07
Updated: 2020-02-07
Packaged: 2021-02-28 01:40:14
Rating: Mature
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 1
Words: 2,953
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/22595671
Author URL: https://archiveofourown.org/users/AndreaDTX/pseuds/AndreaDTX
Summary: A simple jab that Dean uses to tease his younger brother, but does Sam really have to be ashamed if there's some truth to it? A character study of the sexual maturation of one Sam Winchester and the series-long struggle with bodily autonomy, consent, and survivorship that created Sam Winchester, Professional Badass/ Resident Zen Master.
Relationships: Amelia Richardson/Sam Winchester, Dean Winchester & Sam Winchester, Jessica Moore/Sam Winchester, Madison (Supernatural: Heart)/Sam Winchester, Ruby/Sam Winchester, Sam Winchester/ OFC, Sam Winchester/ OMC
Comments: 6
Kudos: 39





	Sam Winchester Cries During Sex

**Author's Note:**

> Okay. This has been in my WIP folder for over two years and I refuse to let it simmer any longer. 
> 
> TW: Deals with the canonical sex life of Sam. Nothing is overly detailed, but if a canon plot line about his sex life rubbed you the wrong, tread carefully. Also, beware of some internal victim blaming on Sam's part as he tries to come to terms with how he feels about the things he's experienced.

Sam Winchester has always been peculiar about sex. Dean calls it weird. Sam prefers… particular. Or maybe discerning? Regardless of how it’s described, sex and everything that goes along with it has just always been and probably always will be a Really Big Deal for Sam.

Honestly, it’s tough to pin down the who, when, what, how or whys of his quirks. They moved so often, it was hard to get a feel for how other kids thought about or acted on it. What he does know for a fact is that he’s always treated it differently from Dean, the only consistent metric Sam’s ever had.

As kids, Sam and Dean are inseparable. It’s an unavoidable part of their nomadic lifestyle and being the only constants in each other’s lives. Not that Sam minds. As far as he’s concerned, Dean hung the sun, the moon, and the stars and he diligently mimics everything his older brother did. Until the summer he turns eight, not long after Dean turns twelve. That’s the year Dean gets weird and goofy and moony-eyed about girls which makes no sense to Sam who’s still deeply in cootie territory. Dean suddenly wants to hang out at the local diner or the rec center or on the bleachers until cheer practice ends. Wherever the girls are, that’s where Dean wants to be. Sam tags along frowning, forever following Dean but completely confused by his big brother’s new obsession.

Time passes and Dean rapidly morphs into an early prototype of the lady-killer he’ll eventually be, baffling Sam even more. He doesn’t get why his brother who used to gleefully search for beetles, crickets, and earthworms with him suddenly hates to get dirty outside of hunting or training. Or why they never walk home from school alone anymore, instead there’s always a (different) giggling girl with them, making them have to take the long way to drop her off wherever she lives.

It’ll be years before Sam got even the slightest inkling of understanding because Sam, of course, is perennially a late bloomer, forever too skinny and too short for his age, making (rude) people wonder out loud how he could possibly be related to Dean who towers at six feet tall by the time he’s sixteen and John who’s even taller. Sam, on the other hand, is still a few inches off the five-foot mark and a dozen pounds short of the buck mark at age thirteen. It leaves him shy and self-conscious, aware of the constant comparisons to his big brother who can turn the heads of college co-eds at seventeen. It’s a self-consciousness that will never really fade even after Sam finally, _finally_ , hits puberty.

Or rather puberty hits him. And knocks him flat on his scrawny ass.

He spends years looking forward to catching up to Dean, to being every bit as handsome, smooth, and effortlessly popular. But apparently that’s wishful thinking. Instead, he ends up an awkward jumble of uncontrollable arms and lanky legs with embarrassing acne and a squeaky voice that refuses to settle. Awkward as a new-born giraffe, he trips over his own feet, hits his head on low hanging light fixtures, runs into things and people. It doesn’t exactly attract attention of the female persuasion. On the contrary, he’s almost always immediately targeted for his general lack of muscle and even worse coordination by half-brained, over macho jocks in nearly every school they land at. Despite his egging jabs, Dean would gladly and thoroughly rip out the spine of anybody who gives Sam a hard time. But Sam never complains. He just wants to fit in. With his family, at school, with the world at large. And complaining doesn’t help you fit in. Admitting that you have no idea how to control your new, freaky body doesn’t make people think you’re cool. So instead of asking Dean for advice like he used to, Sam grows intensely private, tightly guarding the true extent of his discomfort, insecurity, and confusion.

The tight quarters that had once been a source of comfort now grate at him. He doesn’t want anyone to know how bad his joints hurt _all the time_ or how he’s growing so fast it’s literally giving him stretch marks despite being rail thin or how often he jerks off (constantly) or has wet dreams (frequently). It doesn’t matter that they’re all guys who live in each other’s back pockets (nearly literally) or that Dean and John being older means they’ve already gone through what Sam’s experiencing. He becomes hypervigilant about his privacy. It isn’t until years later that Dean disabuses him of his delusion, telling him that the borderline-ridiculous lengths of time in the bathroom with the sink or shower running and a sudden obsession with clean laundry ratted him out without Sam ever saying a word. But neither Dean nor John are crazy enough to do more than tease Sam who’s loathe to admit when he doesn’t know something. They know the very obvious: Sam’s the last of the Winchester clan to go through puberty, the only one who hasn’t figured it out yet, and it irritates him to no end.

To avoid being judged, Sam projects, turning into a mouthy, judgmental asshat. More often than not, Dean is his favorite target, convenient and seemingly unfazed by the criticism. He picks and picks at Dean, throwing around words like ‘lubricious’ and ‘libertine.’ Dean laughs it off, lets Sam get his jabs in. After all, to complain, Sam has to talk which Dean considers worth the price of admission since it lets him keep tabs on what’s going on in his brother’s nerdy little head.

Still, despite the intense focus required to keep Sam happy(-ish) and healthy, Dean wouldn’t have even known when Sam cashed in his v-card, if not for noticing that one his rubbers had gone missing.

_Hey, Sammy. Weird question, but my stash is a rubber short. I know I had four more. Now, I only got three. You know what happened to other one?_

_How would I know? You probably used it and forgot about it._

Complete and utter bullshit. Sam has no way of knowing, but Dean didn’t actually lose his virginity until a little over two months after his seventeenth birthday. He might treat Dean like a man whore, but truth is, at twenty, Dean’s only recently cracked into the double digits and would know exactly when and with whom he’d used a rubber. If he’s right about the condom, Sam beat his start by an entire year. Because of a few awkward but candid ‘don’t do anything stupid’ conversations on back roads, Dean knows Sam beat their dad by nearly two.

When Dean shares his suspicions with his dad, John only chuckles.

_Wouldn’t be Sammy if he wasn’t outdoing us both, huh?_

Sam balks at the box of condoms John buys him and never even cracks the seal. Maybe Sam finds his own supply or maybe decides he’ll wait before he does an encore. Dean doesn’t really know. But nobody turns up pregnant or diseased so it’s whatever.

* * *

College is a liberation that gives Sam a kindred spirit’s appreciation for the 70s and the age of free love no matter how many times he’s heard his dad mutter about ‘those damned hippies.’ Once on campus, Sam pushes himself beyond his near crippling shyness, determined to make the most of it. At Stanford, he finally has the chance to be himself. He isn’t John Winchester’s runt son or Dean Winchester’s kid brother. People look at him and they see Sam Winchester. And apparently, they like what they see.

The first time he gets hit on by a girl, Marla, they’re talking at a party. Somehow, talking leads to drinks and drinks lead to sitting on a couch with her straddling his lap and grinding against him until they both come, their shivers and sighs hidden in the low light of the room and the music blasting from the stereo. The first time he gets hit on by a guy, Owen, he doesn’t know what to think. But he knows he isn’t disgusted as Owen pushes into his personal space or when he feels the hard heat of Owen pressing against his belly. The encounter ends with Owen blowing Sam until his brains nearly melt and leak out of his cock into that amazing mouth. It might’ve gone farther if he hadn’t met Jess three days later.

Jess loves him, genuinely enjoys every facet of his personality. The awkward shyness, the insatiable sexual appetite, the relative inexperience, the open-mindedness. She takes great delight in blowing his mind, in blowing through his firsts: the first person to finger him, to rim him, to stick a vibrator up his ass and then suck his dick until he forgets his name and can barely remember to breath. Combined with her academic drive and her support for his professional dreams, she’s perfect. He plans to spend the rest of their lives together.

The rest of her life ends up being two years and change.

Although he never says it out loud, Sam more or less takes a vow of celibacy following Jess’ death. No one will ever be able to replace her and he can’t even consider anybody else until he makes that bastard demon pay. Dean totally understands, even if he makes sure Sam has ample opportunities available if and when he ever gets back in the saddle. There’s Lori Sorenson when they work the Hook Man case, but it’s way too soon for either Lori or Sam after the loss of the person they were dating. Soon after, Sam meets Meg, who at the time hadn’t seemed possessed, but luckily Sam was so focused on the fight he was having with Dean and his dad that he missed the clear signals Meg was sending. His head’s a little clearer by the time they meet Sarah. In another life, that might’ve really gone somewhere. Somewhere with a white picket fence, 2.5 kids, and a dog named Odysseus (Odie for short).

Before Sam can decide what he wants, Meg forcibly takes his body for a spin. The things Meg does to him, makes him do, will still make him sick to his stomach months later. Chugging bottles of cheap alcohol. Chain smoking entire packs of cigarettes. Binging on shitty fried foods. The longer she has him the crueler and more sadistic she got, not only hurting him from the inside, but striking out at others. Killing the hunter, the feel of life slipping from between his fingers. Shooting Dean. Attacking random people.

And it got worse.

Sam must be the first male vessel she’s had because she seems utterly fascinated by his body’s responses to sexual stimuli and is apparently determined to milk the experience for everything it was worth. Her favorite seems to be edging, pushing Sam to the forefront of his mind just as his body’s trembling on the edge of orgasm, keeping him there while she controls his limbs and teases him, only to snatch him back just as he peaks so that he doesn’t experience the relief of release. She doesn’t seem to tire of that even after his body starts to interpret the unabated arousal as painful rather than pleasurable. By the time she’s finally exorcised, Sam’s dirty and thoroughly used in unfamiliar places, uncomfortable and uncertain what has been done to and with his body during the times Meg shoved him to the dark corners of his own mind. He’s not sure he even wants to know.

He does, however, remember Jo. He vividly remembers menacing her, restraining and touching her in ways that clearly made her uncomfortable, even if Meg never had the chance to physically cross the line as far as he knows. He never gets back the memories of the missing time, but if Meg could make him kill a fellow hunter, attack Jo, Bobby, and his brother, and have him smoking like a chimney, what else might she have done with his body without his permission? Not knowing ratchets his sex and body neurosis through the roof. For months, just as he’s falling asleep, he gets a sense memory of being touched and it makes him feel immeasurably afraid.

By the time they meet Madison, Sam just wants a pure physical connection, something to write over the bad memories. Madison’s beautiful and charming. To top it off, she’s smart, even works for a law firm. She’s physically different enough from Jess to try.

The temporary physical relief is in no way worth the pain that follows.

* * *

After that, he mostly keeps to himself. It’s just not worth it. Any woman who makes the mistake of liking Sam Winchester is instantly doomed. For months, years, he takes care of his needs furtively in the shower. Occasionally, if Dean indicates he’s found company and tells Sam not to wait up, he draws it out, longer jerk off sessions with his body strewn across his motel bed. He convinces himself it’s enough, that he doesn’t need anything. The tenuous self-isolation works.

Until Dean dies.

Rudderless. Unmoored. Alone.

Ruby swoops in. Exploits that lack of connection. In hindsight, he can admit it was brilliant. She can’t replace his brother, but she can become his lover. Offer him precious relief and unparalleled power, swirled all into one. The thrill of the demon blood blows all the shackles off his repressed sexual urges. That delicious freedom, the kind he hasn’t had since those innocent days in college, blinds him. Keeps him from seeing straight, from seeing the truth, even once his beloved brother returns.

_She’s a demon, Sam,_ he’d snarled, judgment dripping from every syllable.

Sam refuses to give up this nirvana, this small bit of omnipotence he’s found. He holds onto it desperately until all hell breaks loose.

* * *

After Sam accidentally releases the devil, Dean forcibly takes command. He’s mean and punitive in a way he’s never been before, having little patience for guilty apologies, making sure Sam can never forget what he’s done for even a moment.

Sam accepts it. He deserves it.

The idea of sex is repulsive. How could it be anything else? He’d willingly stuck his penis inside a possessed, mentally vegetative corpse and drank its blood at the behest of a vixen demon. He wanted to puke every time he thought about it and couldn’t imagine being intimate with another living being ever again.

Gary Frankle has no such compunction. Sam knows for a fact that Gary had sex with some random dominatrix chick while in Sam’s body. Dean admits as much when Sam’s left trying to figure out why he has scratch marks and hickies. It’s shades of Meg all over again. But this time, Sam can’t even find it in himself to be outraged. He settles numbly and without complaint back into his self-imposed celibacy.

* * *

Robo-Sam has sex with any takers that interest him. He doesn’t sleep, eats only for survival, and exercises like a fiend. But without Sam’s trauma-ladened soul to dampen his libido, his body decides it’s time to make up for lost time. Once again, his body is taken for a ride without him at the wheel. But this time, it’s not a demon or rogue witches. It’s Sam’s own baser instincts. In hindsight, Sam wonders if that’s who he really is.

He wonders up until he hits a dog.

He can never explain it to Dean. It’s inexplicable. The draw is that Amelia doesn’t want anything. She doesn’t even really want Sam. She likes his company, sure. But he’s a placeholder for her just like she is for him. They’re miserable in the same way. When they finally have sex, he pretends not to see her tears. Afterwards, she politely does the same for him. When Don and Dean both return, he finally realizes the truth. That’s why he walks away, leaves Amelia to her apple pie life.

It was never about sex. It was always about being connected.

* * *

Fate always seems to be angling to make him feel lonely, like there’s no one else out there to tether him.

Crowley kills Sarah just to fuck with them. Sam never had sex with her and the nascent crush had faded long ago.

He’s devastated nonetheless.

He can’t lose any more friends.

Dean tricks him into sharing his body with an angel who then hijacks the whole shebang and uses him to murder their friend.

It’s the one thing he’d always trusted his brother would never do, the unforgivable sin. And for a long time, Sam can’t imagine how he’ll ever forgive the betrayal.

But he can’t lose his brother, his only family.

Lady Toni kidnaps and tortures him, uses magic to fuck with his head. She’s so proud of her sex illusion. When Sam comes back to himself, shaky, his pants filthy and jizzed out, he laughs. She can’t control him with sex. Stronger people have tried and failed. He resists her at every turn.

He can’t lose himself. What’s left after that?

In the end, he survives. (He always does.) He has his brother. (He always will.) There will be others, some genuine, some malicious, some nameless good times. Sam looks for connections in other ways, friends, family, allies, and vows to stop allowing sex to be such a Really Big Deal.

He’ll never be like Dean, completely willing to go with the flow. His life is his life, his past is his past. It never really goes away. But now, with age and experience, he’s more comfortable in his own skin. He can accept it:

Sam Winchester will always be peculiar about sex.

**Author's Note:**

> Question: With Dean having a contrasting attitude toward sex and very different sexual experiences, would you be interested in a similar character study about him? I have also considered a distinct and separate one for Castiel who has had several run ins with human sexuality.


End file.
